SA516371620B1 - Heterometallic catalysts and mixtures thereof - Google Patents
Heterometallic catalysts and mixtures thereof Download PDFInfo
- Publication number
- SA516371620B1 SA516371620B1 SA516371620A SA516371620A SA516371620B1 SA 516371620 B1 SA516371620 B1 SA 516371620B1 SA 516371620 A SA516371620 A SA 516371620A SA 516371620 A SA516371620 A SA 516371620A SA 516371620 B1 SA516371620 B1 SA 516371620B1
- Authority
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- Saudi Arabia
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- aaa
- group
- Prior art date
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- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 11
- 150000002118 epoxides Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- 239000001569 carbon dioxide Substances 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- -1 nitrate halide Chemical class 0.000 claims description 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000012986 chain transfer agent Substances 0.000 claims description 4
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 239000003426 co-catalyst Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical group [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 150000007855 nitrilimines Chemical class 0.000 claims description 2
- UUZZMWZGAZGXSF-UHFFFAOYSA-N peroxynitric acid Chemical compound OON(=O)=O UUZZMWZGAZGXSF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 241000282941 Rangifer tarandus Species 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003368 amide group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 150000004820 halides Chemical group 0.000 claims 3
- 230000003647 oxidation Effects 0.000 claims 3
- 238000007254 oxidation reaction Methods 0.000 claims 3
- 101100021573 Caenorhabditis elegans lon-8 gene Proteins 0.000 claims 2
- 241001492658 Cyanea koolauensis Species 0.000 claims 2
- 101100346656 Drosophila melanogaster strat gene Proteins 0.000 claims 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 claims 2
- DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 claims 2
- 239000002879 Lewis base Substances 0.000 claims 2
- 102100034184 Macrophage scavenger receptor types I and II Human genes 0.000 claims 2
- 101710134306 Macrophage scavenger receptor types I and II Proteins 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- 241000283011 Rangifer Species 0.000 claims 2
- 108010056243 alanylalanine Proteins 0.000 claims 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 2
- 150000007527 lewis bases Chemical group 0.000 claims 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 241001093575 Alma Species 0.000 claims 1
- 101100172118 Caenorhabditis elegans eif-2Bgamma gene Proteins 0.000 claims 1
- 101001028732 Chironex fleckeri Toxin CfTX-A Proteins 0.000 claims 1
- 229910020598 Co Fe Inorganic materials 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 241000989913 Gunnera petaloidea Species 0.000 claims 1
- 240000008415 Lactuca sativa Species 0.000 claims 1
- 101100229738 Mus musculus Gpank1 gene Proteins 0.000 claims 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims 1
- 241000036848 Porzana carolina Species 0.000 claims 1
- 101000882573 Rattus norvegicus Estrogen receptor Proteins 0.000 claims 1
- 235000014548 Rubus moluccanus Nutrition 0.000 claims 1
- 235000018734 Sambucus australis Nutrition 0.000 claims 1
- 244000180577 Sambucus australis Species 0.000 claims 1
- 241000568452 Sania Species 0.000 claims 1
- 229910009369 Zn Mg Inorganic materials 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- 238000011955 best available control technology Methods 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000005056 cell body Anatomy 0.000 claims 1
- 235000013367 dietary fats Nutrition 0.000 claims 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
- 239000010520 ghee Substances 0.000 claims 1
- 125000006492 halo alkyl aryl group Chemical group 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000010977 jade Substances 0.000 claims 1
- 235000013372 meat Nutrition 0.000 claims 1
- 229910052754 neon Inorganic materials 0.000 claims 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 235000012045 salad Nutrition 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000003375 sulfoxide group Chemical group 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 abstract description 3
- 229910052725 zinc Inorganic materials 0.000 abstract description 3
- 230000002950 deficient Effects 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- XTUSLLYSMVWGPS-UHFFFAOYSA-N carbonic acid;cyclohexene Chemical compound OC(O)=O.C1CCC=CC1 XTUSLLYSMVWGPS-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
- 239000003863 metallic catalyst Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- XAHFLIZFJPTOTF-UHFFFAOYSA-N carbonic acid;hexane Chemical compound OC(O)=O.CCCCCC XAHFLIZFJPTOTF-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- PIFBJINVDJJYCV-UHFFFAOYSA-J dizinc tetraacetate Chemical compound [Zn+2].[Zn+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O PIFBJINVDJJYCV-UHFFFAOYSA-J 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/32—General preparatory processes using carbon dioxide
- C08G64/34—General preparatory processes using carbon dioxide and cyclic ethers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
- B01J2531/0216—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/22—Magnesium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/31—Aluminium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
يتعلق الاختراع الحالي بمحفزات جديدة بالصيغة (I)، حيث M1 وM2 تكون مختلفة وتكون منتقاة بشكل مستقل من Mg، Zn، Fe، Co، Al وCr وانظمة المحفز التي تضم هذه المحفزات. ويتعلق الاختراع باستخدام المحفزات المبتكرة وانظمة المحفز لتحفيز التفاعل بين (i ثاني اوكسيد الكربون والايبوكسيد، (ii ايبوكسيد وانهيدريد، او (iii لاكتيد و/ أو لاكتون. ويتعلق الاختراع بطريقة لإنتاج محفز بصيغة (I). شكل 1The present invention relates to novel catalysts of Formula (I), wherein M1 and M2 are different and are independently selected from Mg, Zn, Fe, Co, Al and Cr and the catalyst systems comprising these catalysts. Fig. 1
Description
١ محفزات معدنية غير متجانسة وخلائط منها1 Heterogeneous metal catalysts and mixtures thereof
Heterometallic catalysts and mixtures thereof الوصف الكامل خلفية الاختراع يتعلق الاختراع الحالي بمجال محفزات البلمرة polymerisation catalysts وبالتحديد محفزات معدنية غير متجانسة heterometallic catalysts وخلائط منهاء وأنظمة تشتمل على المحفزات المذكورة لبلمرة ثاني أكسيد الكربون (CO,) carbon dioxide وايبوكسيد «epoxide © لاكتيد lactide و/ أو لاكتون dactone أو إيبوكسيد وأنهيدريد .anhydride أثارت المشاكل البيئية والاقتصادية المرتبطة باستتفاد مصادر الزيت أهمية متزايدة في التحول الكيميائي لثاني أكسيد الكربون؛ حتى تتيح استخدامها على هيئة مصدر كربون carbon source متجدد. يكون ثاني أكسيد الكربون؛ بالرغم من انخفاض 4 تفاعليته؛ عبارة عن خام تغذية كربون carbon feedstock جذاب بشكل dle حيث يكون غير مكلف؛ غير سام lee متوفر بوفرة Ve بنقاء عالي وغير خطير. لذلك؛ يمكن أن يكون ثاني أكسيد الكربون عبارة عن بديل واعد للمواد Jie أول أكسيد الكربون carbon monoxide وفوسجين phosgene في عمليات كثيرة. تكون إحدى تطبيقات التطوير لثاني أكسيد الكربون هي البلمرة المشتركة باستخدام إيبوكسيدات 5 للحصول على بولي كربونات أليفاتية polycarbonates ©810081؛ مجال رائد Inoue ef al. more than 40 years ) أكثر من 50 عام مضى .Inoue et al بواسطة .ago (Inoue, 5. etal J. Polym. Sci., Part B: Polym. Lett. 1969, 7, pp287 ٠٠ في براءة الاختراع الدولية رقم OY EV [Ye 0d يتم تضمين محتوياتها بالكامل في هذه الوثيقة كمرجع؛ تم وصف البلمرة المشتركة لإيبوكسيد مع ثاني أكسيد الكربون باستخدام محفز catalyst من فئة ممثلة بواسطة الصيغة (ا): حضفتHeterometallic catalysts and mixtures thereof Full description BACKGROUND The present invention relates to the field of polymerisation catalysts, specifically heterometallic catalysts, terminator mixtures and systems comprising said catalysts for polymerization of carbon dioxide (CO,) and epoxide “epoxide” © lactide and/or dactone or epoxide and anhydride . Environmental and economic problems associated with the utilization of oil resources have given rise to increasing importance in the chemical transformation of carbon dioxide; In order to allow it to be used as a renewable carbon source. be carbon dioxide; 4 Although its reactivity is low; It is a carbon feedstock that is dle attractive as it is inexpensive; Non-toxic lee is abundantly available Ve in high purity and non-hazardous. So; Carbon dioxide can be a promising alternative to materials Jie carbon monoxide and phosgene in many processes. One development application of CO2 is copolymerization with 5 epoxides to obtain polycarbonates ©810081; Leading field Inoue ef al. more than 40 years) Inoue et al. by .ago (Inoue, 5. etal J. Polym. Sci., Part B: Polym. Lett. 1969, 7, pp287 in International Patent No. OY EV [Ye 0d The entire contents of which are incorporated herein by reference; Copolymerization of an epoxide with carbon dioxide is described using a catalyst of a class represented by formula (a): insert
— اذ Ry RoR » Eq XE NR, 2 يلا ~ ا TN, ال <- ص وملا ELS ل Ea لام Eq © R; ( من بين الإيبوكسيدات epoxides المستخدمة في البلمرة المشتركة؛ يوضح سيكلو هكسين أكسيد (CHO) cyclohexene oxide الذي لاقى اهتمام (ala على هيئة المنتج؛ بولي A) هكسين كربونات) (PCHC) poly(cyclohexene carbonate) درجة حرارة تحول الزجاج glass transition temperature © ومقاومة شد معقولة. لاقى أكسيد البروبيلين Propylene af oxide اهتمام حيث ينتج بوليمر polymer (بولي بروبيلين كربونات polypropylene ig 20 «carbonate ب (PPC بخواص مرنة حيث تكون مفيدة في تطبيقات رقيقة. سجل Angew.— As Ry RoR » Eq XE NR, 2 yla ~ a TN, the <- p and mL ELS for Ea l Eq © R; Among the epoxides used in copolymerization, the cyclohexene oxide (CHO) of interest has been shown (ala in product form; poly A) hexane carbonate (PCHC) poly( cyclohexene carbonate) glass transition temperature© and reasonable tensile strength. Propylene af oxide has received interest as a polymer (polypropylene ig 20 “carbonate b) PPC with elastic properties that are useful in thin applications. Angew.
Chem., Int.Chem., Int.
Ed., 2009, 48, 00931 and /norg.Ed., 2009, 48, 00931 and /norg.
Chem., ( Kember et al ,486 ,2009( معقد داي أسيتات زنك acetate complex 01-2106 مستقر في ٠ الهواء» منسقة بواسطة مركب ترابطي حلقي كبير ligand 16ا071801007/0؛ يقع داخل الصيغة )1( Del حيث توضح نشاط حفزي عالي؛ حتى عند ضغط ثاني أكسيد الكربون محيط. يظهر المحفز انتقائية بلمرة مشتركة ممتازة؛ تعطي نسبة عالية من وحدات الكربونات المتكررة carbonate repeat units وحصيلات منخفضة من المنتج الثانوي سيكليك سيكلو هكسين كربونات cyclic (CHC) cyclohexene carbonate يكون معقد داي- زنك أسيتات عبارة عن مثال نادر Vo للمحفز حيث يكون قادر على النشاط اعالي عند الضغط المحيط ١( بار) من ثاني أكسيد الكربون؛ polydispersity index ضيق «(PDI) والوصول بشكل ملحوظ إلى أعداد دوران turnover 35 عالية .(TON) تكشف براءة الاختراع الدولية رقم Al NY ممح كي التي يتم تضمين محتوياتها في هذه الوثيقة ٠ بالكامل كمرجع؛ عن البلمرة المشتركة لإيبوكسيد باستخدام ثاني أكسيد الكربون في وجود عامل نقل سلسلة chain transfer agent باستخدام محفز من فئة ممثلة بواسطة الصيغة (ا): TEChem., (Kember et al., 2009, 486) Zinc acetate complex 01-2106 is stable in “0 air” coordinated by a large cyclic ligand ligand 16a071801007/0; located within formula (1) Del demonstrates high catalytic activity even at ambient CO pressure The catalyst exhibits excellent copolymerization selectivity, yielding a high percentage of carbonate repeat units and low yields of the cyclic by-product (CHC) cyclohexene carbonate complex di-zinc acetate is a rare example Vo of a catalyst that is capable of higher activity at ambient pressure (1 bar) of CO2; narrow polydispersity index (PDI). ) and attaining remarkably high turnover numbers of 35 (TON). The Al NY International Patent No. 0 of which the contents of this document are incorporated in its entirety for reference discloses the copolymerization of an epoxide using carbon dioxide in the presence of a chain transfer agent using a catalyst of a class represented by formula (a): TE
— ¢ — Ry > , Rs ب Rs Eq يكلا ? 1 X اس لحي ص اصح ارا x | 6 Eq Sewn NS و Rj 0( ّ تم اختبار المركبات المختلفة وفقاً الصيغة (ا) أعلاه لتحديد قدرتها على تحفيز التفاعل بين الإيبوكسيدات المختلفة وثاني أكسيد الكربون. في كل من تلك المحفزات المختبرة» كل ظهور من M يكون متشابه HLS) لها هنا Lad يلي بمحفزات معدنية متجانسة .(homometallic catalysts © بالرغم من أن براءة الاختراع الدولية رقم 9756/7017 ١7 تتوقع أن المحفزات تشتمل على معدنين مختلفين (يشار لها هنا Lad بعد بمحفزات معدنية غير متجانسة) يمكن استخدامها؛ بحيث لا يتم اختبار تلك المحفزات. N =<) 0 ا عون | I< or oY غير متوقع أن 0 ٠ ذدات المعدنية غير 1 - : انسة تكون Po أيضاً على هيئة المحفزات؛ ولها نشاط حيث يتناسب مع؛ أو أفضل من أي محفزات معدنية متجانسة ٠ > مقابلة منفردة أو كخليط من ٠ :*٠ منها. على سببيل (JB اكتشضف المخترعون أن المحفز المحتوي على مركز معدن metal centre زنك zine وماغنسيوم magnesium يكون له بشكل غير متوقع نشاط أفضل من نشاط المحفزات المقابلة ذات داي زنك أو داي ماغنسيوم؛ أو خليط ٠ 0 من المحفز المقابل ذو داي- زنك 01-2106 وداي ماغنسيوم 01-1089065077. تحتفظ المحفزات المعدنية غير المتجانسة المبتكرة والأنظمة التي تشتمل على ذلك المحفز أيضاً بشكل ٠ غير متوقع بانتقائيتها ودرجة من التحكم فوق البوليمر polymer المنتج. بالتالي؛ Jue الاختراع الحالي اختيار جديد ومبتكر فوق كشوفات المجال السابق. الوصف العام للاختراع في السمة الأولى من الاختراع؛ يتم توفير محفز بالصيغة )1( Tr— ¢ — Ry > , Rs b Rs Eq No ? X | 6 Eq Sewn NS and Rj 0) Different compounds were tested according to formula (a) above to determine their ability to catalyze the reaction between different epoxides and carbon dioxide. In each of these tested catalysts, each appearance of M is homologous (HLS) has here Lad followed by homometallic catalysts ©. Here Lad (with non-homogeneous metallic catalysts) can be used so that these catalysts are not tested. N = <) 0 A | I< or oY Unexpected that 0 , 0 metal thiats other than 1 - : Ms. Po is also in the form of catalysts; And it has an activity where it is commensurate with; or better than any 0 > corresponding metal homogeneous catalysts singly or as a mixture of 0:*0 thereof. By way of (J.B.) the inventors discovered that a catalyst containing a metal center of zine and magnesium had unexpectedly better activity than the corresponding catalysts with di-zinc or di-magnesium; or a mixture of 0 0 of the corresponding catalyst with Di-Zinc 01-2106 and Di-Mg 01-1089065077. Innovative hetero-metallic catalysts and systems comprising this catalyst also unexpectedly retain 0 selectivity and a degree of control over the produced polymer. The present invention is a new and innovative choice over the disclosures of the previous field General Description of the Invention In the first feature of the invention, a catalyst of formula (1) Tr is provided
Qo _ _ Ry يم > Ro Rs Z Rs Eq ويا ? 1 0 re Rn] ~~) aq, 2 1 يقي Se G X Eq Sew NS Ry Ro Ry 0 حيث: ا 3 My, تكون مختلفة وتكون منتقاة بشكل مستقل من «Zn (Mg ول ¢Cry Al «Co Ry ويا تكون منتقاة بشكل مستقل من هيدروجين chydrogen هاليد chalide مجموعة نيترو nitro © مجموعة نيتريل «nitrile إيمين (mine أمين amine مجموعة إيثر ether مجموعة سيليل «silyl مجموعة سيليل إيثر ether الااأ5» مجموعة سلفوكسيد cSUlfOXide مجموعة سلفونيل sulfonyl مجموعة سلفينات sulfinate أو مجموعة أسسيتيليد acetylide أو ألكيل alkyl بها استبدال اختياري» ألكنيل calkynyl Jui calkenyl هالو ألكيل chaloalkyl أريل ال81؛ أريل غير متجانسة cheteroaryl ألكوكسي alkoxy أريل أوكسي Ji caryloxy ير «alkylthio ٠ أريل ثيو carylthio مجموعة ناقصة الحلقة أو ناقصة الحلقة غير متجانسة؛ Ry تكون منتقاة بشكل مستقل من ألكيلين alkylene بها استبدال اختياري؛ ألكنيلين «alkenylene ألكينيلين calkynylene ألكيلين غير متجانسة cheteroalkylene ألكنيلين غير متجانسة cheteroalkenylene ألكينيلين غير متجانسة cheteroalkynylene أريلين carylene أريلين غير متجانسة heteroarylene أو سيكلو ألكيلين ccycloalkylene حيث ألكيلين «alkylene Yo ألكنيلين calkenylene ألكينيلين calkynylene ألكيلين غير متجانة heteroalkylene الكنيلين غير متجانسة heteroalkenylene وألكينيلين غير متجانة «heteroalkynylene يمكن أن تكون مقتطعة اختيارياً بواسطة أريل؛ أريل غير متجانسة؛ ناقصة الحلقة أو ناقصة الحلقة غير متجانسة؛ TF nq أو اختيارياً أليفاتية بها استبدال؛ أليفاتية غير متجانسة؛ Hope تكون منتقاة بشكل مستقل Ry غير متجانسة؛ أريل؛ أريل غير متجانسة؛ ألكيل أريل غير متجانسة dala ناقصة الحلقة؛ ناقصة calkylaryl أو الكيل أريل alkylheteroaryl أليفاتية غير متجانسة؛ ناقصة الحلقة؛ ناقصة الحلقة (Jaga) هي لا أو اختيارياً أليفاتية بها Rs أريل غير متجانسة؛ ألكيل أريل غير متجانسة أو ألكيل أريل؛ dof غير متجانسة؛ © أو را هي لا ررح هي 0؛ NH وا هي 0 5 أو «C را هي تا"ارو)ق (OSO(R*), 4ا050. (OSO,R* <OC(O)R* تكون منتقاة بشكل مستقل من X hydroxyl هيدر كيل «nitrate نيترات chalide هاليد «phosphinate +0؛ فوسفينات أو اختيارياً أليفاتية بها استبدال؛ أليفاتية amido saul camino أمينو «carbonate كربونات غير متجانسة؛ ناقصة الحلقة؛ ناقصة الحلقة غير متجانسة؛ أريل أو أريل غير متجانسة؛ Vo »ا هي بشكل مستقل هيدروجين؛ أو اختيارياً أليفاتية بها استبدال» هالو أليفاتية؛ أليفاتية غير ألكيل أريل أو أريل غير متجانسة؛ و eda) متجانسة؛ ناقصة الحلقة؛ ناقصة الحلقة غير متجانسة؛ أنيوني ile متعادل أو ligand أو منتقاة بشكل مستقل من مركب ترابطي dle تكون ©Qo _ _ Ry yum > Ro Rs Z Rs Eq O ? 1 0 re Rn] ~~) aq, 2 1 Se G X Eq Sew NS Ry Ro Ry 0 where: A 3 My, different and selective independently from “Zn (Mg) and ¢CryAl”CoRy and independently selected from the chydrogen hydrogen halide chalide nitro group nitrile group “nitrile imine” (mine Amine amine ether group silyl group “5-silyl ether” group cSUlfOXide group sulfonyl group sulfinate group or acetylide group or alkyl group has an optional substitution “alkynyl Jui calkenyl haloalkyl chaloalkyl aryl 81 heteroaryl cheteroaryl alkoxy aryl oxy Ji caryloxy yer” alkylthio 0 arylthio carylthio deficient group or deficient heterocyclic ring; Ry is independently selected from an alkylene with an optional substitution; alkenylene “alkenylene” calkynylene heterocyclic cheteroalkylene heteroalkylene cheteroalkenylene heteroalkynylene cheteroalkynylene Ariel carylene heteroarylene or cycloalkylene where alkylene “alkylene yo” calkenylene calkynylene alkylene heteroalkylene heteroalkenylene alkenylene heteroalkenylene heteroalkynylene can be optionally cleaved by an aryl; aryl heterocyclic; hypocyclic or heterocyclic hypocyclic; TF nq or optionally aliphatic with substitution; Heterocyclic Aliphatic; Hope to be independently selected Ry Heterocyclic; ariel; aryl heterocyclic; alkyl aryl heterocycle dala deficient ring; deficient calkylaryl or alkylaryl alkylheteroaryl heterocyclic; incomplete loop Cyclic deficient (Jaga) is neither or optionally aliphatic with heterocyclic aryl Rs; Heterocyclic alkyl aryl or alkyl aryl; dof heterocyclic; © or Ra is anhydrous is 0; NH is 0 5 or “C” is “ta” (s) (OSO) R*), 4A050. (OSO,R* <OC(O)R*) to be independently selected from X hydroxyl nitrate chalide phosphinate +0; or optionally aliphatic with substitution; aliphatic amido saul camino amino carbonate heterocyclic; aryl or heteroaryl; Vo is independently hydrogen; or optionally aliphatic with halo substitution; aliphatic non-alkyl aryl or hetero-aryl; and eda) homocyclic; deficient; deficient heterocyclic; anionic; neutral or ligand or independently selected from a compound associative dle be ©
Lewis حيث يكون عبارة عن قاعدة anionic donor يشتمل على محفز وفقاً من catalyst system في سمة ثانية من الاختراع؛ يتم توفير نظام محفز Vo .co—catalyst السمة الأولى واختيارياً محفز ثاني و/ أو محفز مشترك (i) في سمة ثالثة من الاختراع؛ يتم توفير عملية لتفاعل (آ) ثاني أكسيد الكربون مع إيبوكسيد؛ في وجود محفز lactone و/ أو لاكتون lactide لاكتيد (iii) وإيبوكسيد؛ أو anhydride أنهيدريد وفقاً من السمة الأولى أو نظام محفز وفقاً من السمة الثانية؛ اختيارياً في وجود عامل نقل سلسلة. تقدم السمة الرابعة من الاختراع منتج من العملية وفقاً للسمة الثالثة من الاختراع. ٠ توفر السمة الخامسة من الاختراع طريقة لتخليق محفز وفقاً من السمة الأولى؛ أو نظام محفز وفقاً تشتمل الطريقة على: Apt) من السمة (Ib) أ) تفاعل مركب ترابطي بالصيغةLewis where it is an anionic donor comprising a catalyst according to a catalyst system in a second feature of the invention; A Vo .co—catalyst catalyst system is provided in the first feature and optionally a second catalyst and/or co-catalyst (i) in a third feature of the invention; A process is provided for the reaction of (a) carbon dioxide with an epoxide; in the presence of a lactone catalyst and/or a lactide lactide (iii) and an epoxide; or anhydride anhydride according to the first character or a catalyst system according to the second character; Optionally in the presence of a chain transfer agent. The fourth feature of the invention provides a product of the process according to the third feature of the invention. 0 The fifth feature of the invention provides a method for the synthesis of a catalyst according to the first feature; or a catalyst system according to the method includes: Apt) of characteristic (Ib) a) ligand complex reaction of the formula
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| GB201514506D0 (en) | 2015-08-14 | 2015-09-30 | Imp Innovations Ltd | Multi-block copolymers |
| GB201515350D0 (en) * | 2015-08-28 | 2015-10-14 | Econic Technologies Ltd | Method for preparing polyols |
| CN105646248B (en) * | 2016-03-09 | 2017-10-24 | 大连理工大学 | One class monokaryon N alkyl β ketimide iron compounds and its preparation method and application |
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| US11691139B2 (en) * | 2019-08-15 | 2023-07-04 | ExxonMobil Technology and Engineering Company | Acid/metal bifunctional catalyst systems produced with carbon coatings |
| US11654421B2 (en) | 2019-08-15 | 2023-05-23 | ExxonMobil Technology and Engineering Company | Metal catalysts with low-alkali metal content and acid/metal bifunctional catalyst systems thereof |
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2016
- 2016-08-07 SA SA516371620A patent/SA516371620B1/en unknown
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| SG11201606414QA (en) | 2016-09-29 |
| MX369748B (en) | 2019-11-20 |
| MY184384A (en) | 2021-04-01 |
| KR20160125400A (en) | 2016-10-31 |
| RU2679611C2 (en) | 2019-02-12 |
| EP3102327B1 (en) | 2018-10-10 |
| CN106536045A (en) | 2017-03-22 |
| RU2016134279A3 (en) | 2018-09-06 |
| AU2015214217A1 (en) | 2016-09-01 |
| BR112016018165A2 (en) | 2017-08-08 |
| AU2015214217B2 (en) | 2018-06-21 |
| CN106536045B (en) | 2020-02-07 |
| RU2016134279A (en) | 2018-03-12 |
| MX2016010145A (en) | 2017-04-13 |
| EP3102327A1 (en) | 2016-12-14 |
| US20160347906A1 (en) | 2016-12-01 |
| JP6557669B2 (en) | 2019-08-07 |
| PL3102327T3 (en) | 2019-04-30 |
| ES2703681T3 (en) | 2019-03-12 |
| JP2017506231A (en) | 2017-03-02 |
| GB201402109D0 (en) | 2014-03-26 |
| PT3102327T (en) | 2019-01-11 |
| WO2015118100A1 (en) | 2015-08-13 |
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